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Cunningham, Williamson County's County Clerk and Circuit Clerk.
During 1855, after Cunningham was named registrar for the federal land office in southeastern Illinois at Shawneetown, Illinois, Ingersoll followed him to the riverfront city along the Ohio River.
In addition to his job as a clerk, he and his brother began their law practice using the name "E. With his earlier mentor Cunningham having relocated back to Marion after the land office's closing during 1856, and Logan's relocation to Benton, Illinois, after his marriage that autumn, Ingersoll and his brother relocated to Peoria, Illinois, where they finally settled during 1857.
Ingersoll was married, February 13, 1862, to Eva Amelia Parker (1841-1923). With the beginning of the American Civil War, he raised the 11th Regiment Illinois Volunteer Cavalry and assumed command. Ingersoll was later captured as a result of a Union skirmish with the Confederates near Lexington, Tennessee on December 18, 1862, then released on his promise that he would not fight again (he resigned as regiment commander on June 30, 1863), which was common practice early in the war.
Later that year, the family settled in Marion, Illinois, where Robert and his brother Ebon Clarke Ingersoll were admitted as lawyers during 1854.
The Madison trial occurred when young Robert was nine years old, and it was the unjust and bigoted treatment his father received which made him the enemy, first of Calvinism, and later of Christianity in its other forms.
Robert Green "Bob" Ingersoll (August 11, 1833 – July 21, 1899) was an American lawyer, a Civil War veteran, politician, and orator of the United States during the Golden Age of Free Thought, noted for his broad range of culture and his defense of agnosticism. Robert Ingersoll was born in Dresden, Yates County, New York. Ingersoll remained for a few months as co-pastor/associate pastor with Finney.
His father, John Ingersoll, was an abolitionist-sympathizing Congregationalist preacher, whose radical opinions caused him and his family to relocate frequently. John Ingersoll substituted as preacher for American revivalist Charles G. The elder Ingersoll's later pastoral experiences influenced young Robert negatively, however, as The Elmira Telegram described during 1890:  Though for many years the most noted of American infidels, Colonel Ingersoll was born and reared in a devoutly Christian household.
During 1853, "Bob" Ingersoll taught a term of school in Metropolis, Illinois, where he let one of his students, the future Judge Angus M. Mc Bane, do the "greater part of the teaching, while Latin and history occupied his own attention".
At some time prior to his Metropolis position, Ingersoll had also taught school in Mount Vernon, Illinois.